5-(3,5-bis(4-chlorophenyl)-4,5-dihydroisoxazole-4-carbonyl)-2-hydroxybenzoic acid

ID: ALA3781436

PubChem CID: 127030433

Max Phase: Preclinical

Molecular Formula: C23H15Cl2NO5

Molecular Weight: 456.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(C(=O)C2C(c3ccc(Cl)cc3)=NOC2c2ccc(Cl)cc2)ccc1O

Standard InChI:  InChI=1S/C23H15Cl2NO5/c24-15-6-1-12(2-7-15)20-19(22(31-26-20)13-3-8-16(25)9-4-13)21(28)14-5-10-18(27)17(11-14)23(29)30/h1-11,19,22,27H,(H,29,30)

Standard InChI Key:  WRPHMMVTDXINNM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    4.2010   -3.2956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.9815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511   -0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531   -1.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2567    0.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3615    1.3842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6819    1.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9901    2.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4154    2.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5328    1.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2247    0.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7994    0.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7206    4.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    5.2598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8602    4.8362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6731    2.3640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4458   -1.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1563   -0.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6557   -0.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4415   -1.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7280   -3.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2285   -3.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.6411   -1.7304    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  4 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 16 20  1  0
 20 21  2  0
 20 22  1  0
 17 23  1  0
  5 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
  9 30  1  0
 27 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3781436

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 456.28

Molecular Weight (Monoisotopic): 455.0327

AlogP: 5.37

#Rotatable Bonds: 5

Polar Surface Area: 96.19

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.66

CX Basic pKa: 1.62

CX LogP: 6.08

CX LogD: 2.84

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.50

Np Likeness Score: -0.09

References

1. Puttaswamy N, Pavan Kumar GS, Al-Ghorbani M, Vigneshwaran V, Prabhakar BT, Khanum SA..  (2016)  Synthesis and biological evaluation of salicylic acid conjugated isoxazoline analogues on immune cell proliferation and angiogenesis.,  114  [PMID:26974382] [10.1016/j.ejmech.2016.02.052]

Source

Source(1):

• Scientific Literature